How many cycling events are coming up in Kentucky?
Kentucky has 7 upcoming events listed, from Sat, August 1, 2026 through Sun, February 21, 2027. The next one is Moonlight Ride Paducah in Paducah.
Kentucky · Ride calendar
Cycling Events in Kentucky
Kentucky rides better than its neighbors get credit for. The Bluegrass country rolls through horse-farm fences and stone walls, and out east the Appalachians and the Red River Gorge throw down steep, wooded climbs on quiet backroads.
Summer is humid and the eastern hills are steeper than the map lets on. But the pavement is often empty, the scenery earns the effort, and spring and fall are close to perfect.
7 upcoming events · 7 organized rides
By the numbers
Standouts in the State
The Kentucky events that stand out on the numbers alone: the soonest start, the lowest listed entry, and the most route options.
Rides by City in Kentucky
Soonest Rides in Kentucky
7 total Sat, August 1, 2026 Moonlight Ride Paducah Paducah, KY From $35 View Event Sat, August 8, 2026 Old Kentucky Home Bicycle Tour (OKHT) Crestwood, KY From $50 View Event Sat, September 19, 2026 Misaligned Minds West Paducah, KY From $50 View Event Thu, September 24, 2026 Bourbon Burn Lexington, KY Free entry listed View Event Sat, October 3, 2026 Cameron Ponder Cycling Classic Elizabethtown, KY From $29.54 View Event Sat, October 10, 2026 Hills & Hollers for Habitat Paducah, KY From $35 View Event Sun, February 21, 2027 2027 PNC Tour de Lou Training Program Provided by Louisville Bicycle Club Louisville, KY Free entry listed View Event
How we build these listings: Event counts, dates, and fees are computed from live registration listings (synced nationally from the RunSignup/BikeSignup platform), deduplicated and filtered to cycling disciplines. We list what is verifiably open for registration — not every ride that exists. Last updated July 19, 2026.
Common Questions About Riding in Kentucky
What does it cost to enter a ride in Kentucky?
Listed entry fees currently run from $0 to $50, depending on the event and route. Check each registration page for current fees and deadlines.
When is the busiest month for cycling events in Kentucky?
August 2026 is currently the busiest month on the Kentucky calendar with 2 listed events.
Riding Somewhere Else?
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